
Retire With Purpose - The Retirement Podcast
Whether you are in retirement or have yet to make the transition, The Retire With Purpose podcast is a show designed to help you maximize your financial confidence and elevate your fulfillment in this chapter of life.
Each week Casey Weade, a CERTIFIED FINANCIAL PLANNER™ and Founder of Howard Bailey Financial, discusses thoughts and ideas with some of today's foremost names in finance and retirement, as well as trending topics that could impact your bottom line. These strategies can help you make better financial decisions so you can live the lifestyle you’ve always imagined and deserve.
Investment Advisory Services may be offered through Howard Bailey Securities, LLC, a registered investment adviser. Working with Howard Bailey Securities, LLC, cannot guarantee investment success or that specific financial goals will be achieved. For more information on professional designations, visit finra.org/investors/professional-designations.
©2024 HOWARD BAILEY FINANCIAL, INC.
Latest episodes

4 snips
Jul 18, 2025 • 28min
511: Sequence Risk Meets RMDs: The Retirement Trap No One Talks About
Are your Required Minimum Distributions (RMDs) a ticking time bomb for your retirement? Discover how RMDs and sequence of returns risk intertwine, potentially jeopardizing financial security. Explore strategies to optimize withdrawals during market shifts, including the value of timely Roth conversions. Learn why asset allocation and withdrawal timing are crucial in mitigating financial fallout. With expert insights, navigate the complexities of RMDs to safeguard your retirement income and maintain peace of mind.

Jul 14, 2025 • 54min
510: Managing Investment Risk When You've Already Won The Game with William Bernstein
William Bernstein, a renowned investment advisor and retired neurologist, shares his wealth of knowledge on managing investment risks for retirees. He argues that money's true purpose is to buy freedom and peace of mind, rather than material goods. Bernstein emphasizes the dangers of continuing to invest after achieving financial goals, discussing deep versus shallow risks. He highlights the psychological aspects of aging in investment decisions and underscores the need for a tailored retirement plan that prioritizes personal fulfillment and meaningful connections.

20 snips
Jul 11, 2025 • 40min
509: Freedom After 50: 7 Practices to Help You Stop Hiding and Start Growing
Les McDaniel, a certified retirement coach, joins Casey Weade to explore personal growth beyond finances as we age. The conversation centers on embracing one’s 'shadow self'—the hidden aspects we often ignore. They discuss how unresolved emotional patterns affect our health and joy, and the importance of self-reflection in retirement. By confronting insecurities and aligning values with actions, listeners can foster deeper connections and find true peace in their second act. Tune in for transformative insights into personal fulfillment.

4 snips
Jul 4, 2025 • 23min
508: More Control, Less Surprise: A Real Retirement Tax Wake-Up Call
What's the biggest surprise in retirement? Fritz Gilbert shares his unexpected challenges with Roth conversions and the impact on his finances. Delve into why planning ahead is crucial, as waiting may lead to more taxes and complications. Discover how strategic conversions can reduce required minimum distributions, Medicare premiums, and even benefits for heirs. This episode emphasizes the importance of proactive tax strategies to navigate uncertainties and ensure a smoother financial journey in retirement.

8 snips
Jun 27, 2025 • 43min
507: Freedom After 50: You’re Not Looking for Advice—You’re Looking for Alignment, Part 2
In this engaging discussion, Certified Retirement Coach Les McDaniel joins Casey Weade to delve into finding alignment over merely seeking advice after 50. They highlight the importance of asking better questions and elevating emotional awareness to foster authentic financial decisions. The duo explores how to break free from draining patterns and envision life goals that transcends routine. They also tackle the intricacies of advice in today’s influencer era and stress the need for self-reflection to lead a meaningful life.

7 snips
Jun 20, 2025 • 23min
506: The Surplus Bucket Strategy: A Way to Spend More Confidently in Retirement
Discover how retirees can manage spending confidently without relying solely on annuities. Learn about the dynamics of underspending and the innovative ‘Surplus Bucket’ strategy to effectively allocate surplus assets. The discussion covers how the funded ratio can influence your income plan and the balance between enjoying savings and leaving inheritances. The importance of personalized financial strategies tailored to individual values is emphasized to enhance overall retirement satisfaction.

22 snips
Jun 13, 2025 • 28min
505: Freedom After 50: You’re Not Looking for Advice—You’re Looking for Alignment, Part 1
Les McDaniel, a certified retirement coach at Howard Bailey Financial, delves into the vital connection between personal experiences and meaningful financial advice. He discusses how understanding your own story can transform generic advice into actionable insights. The conversation highlights the challenges of advice overload and emphasizes aligning financial goals with personal values. Listeners gain a practical framework for navigating their retirement journey with clarity and purpose, moving from seeking advice to achieving genuine alignment.

24 snips
Jun 9, 2025 • 48min
504: How to Stay Sharp and Prevent Cognitive Decline in Retirement with Dr. Ross Andel
Dr. Ross Andel, a gerontologist and professor at Arizona State University, dives into the crucial link between retirement and cognitive health. He discusses how retiring from high-level careers can increase cognitive decline and emphasizes the need for purpose-driven post-retirement activities. His research highlights the benefits of volunteering and new hobbies in enhancing brain function. Additionally, Dr. Andel addresses the importance of sleep, lifestyle choices, and self-care for those caring for loved ones with dementia.

Jun 6, 2025 • 17min
503: Investing at the Sleeping Point: Finding Peace in Your Portfolio
After a sharp rebound in the market, you may still feel the lingering effects of recent volatility. But before the next tide of turmoil, now is an ideal time to deploy the "Sleeping Point" Strategy: adjusting your portfolio to a level where you can sleep soundly at night. In this episode, we discuss: The importance of reducing risk before panic How to embrace proactive planning The danger of over-investing How (and when) to stress test your portfolio Today's article is from Pearl's Prime Cuts blog titled, A Good Time for the Sleeping Point Story. Listen in as Founder and CEO of Howard Bailey Financial, Casey Weade, breaks down the article and provides thoughtful insights and advice on how it applies to your unique financial situation. Show Notes: HowardBailey.com/503 📧 WEEKEND READING FOR RETIREES: Receive CFP® insight on 4 hand-picked financial articles delivered straight to your Inbox each Friday: https://bit.ly/3OEdGgu 📅SCHEDULE YOUR PERSONAL FINANCIAL REVIEW: Book a 15-minute call with Howard Bailey Financial to see how the topics discussed here apply to your individual situation: https://bit.ly/3T6oNDB ABOUT HOWARD BAILEY FINANCIAL: Our mission is to help others gain clarity in purpose and elevate meaning in their lives through personal and practical financial strategies. Our Retire With Purpose™ Framework starts with establishing your unique financial philosophy — the true meaning and purpose for your money in retirement. Through continued education, one-on-one meetings, and a comprehensive team planning approach, we have helped retirees across the country secure their financial futures. And while we can't work with everyone, our goal is to provide value to everyone we meet. Our team of advisors and support specialists strive to deliver the very best experience in pre-retirement and retirement planning. Learn more about our process here: https://howardbailey.com/our-process

17 snips
May 30, 2025 • 28min
502: Freedom After 50: The Hidden Cost of Delayed Gratification in Retirement
Les McDaniel, a certified retirement coach at Howard Bailey Financial, joins the discussion on how a lifetime of delayed gratification can become a hurdle in retirement. He explores the psychology behind postponement and the importance of shifting from saving to enjoying life. The concept of a 'joy budget' is introduced, offering tools to reframe spending and enhance personal fulfillment. Listeners learn about the balance between enjoyment and savings while uncovering strategies for personal growth and connection through tradition and heirlooms.